Same problem here
My original headset didnt work but dmesg:

headphone (GPIO 177) is now connected <-when i conect original headset
headphone (GPIO 177) is now disconnected <- when i disconnect headset

but i dont see icon in systray and no soudn or working buttons on headset

When i connect headphones alone i got same mesage + icon in systray
and sound works

So where is problem ? i think is SW
BTW: i can give ssh or vnc acces to maemo developers who would want to find out what it is and how to fix it
PS:My tv-out cable works fine